Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu
{"title":"Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation","authors":"Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu","doi":"10.1055/a-2204-8921","DOIUrl":null,"url":null,"abstract":"Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis-Stuttgart","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2204-8921","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.
期刊介绍：
SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
